Kaleem Caire, founder and CEO of One City Schools, gets a little emotional talking about the One City Schools kindergarten graduation ceremony that was held at his childhood park – Penn Park – for the very first time.

“I was walking up to Penn Park and walked in front of my own townhouse where I grew up at 2130 Fisher St. on the corner and I turned around and saw the kids coming up the street in a straight line in those gold cap and gowns,” he says. “I was like, ‘Holy moly.’ It really hit me. They walked right to the very entrance where Gregory Henderson was shot and killed. That was such an emotional thing, brother.”

One City has held kindergarten graduation ceremonies in previous years, but this most recent one on July 30 at Penn Park brought everything full circle for Caire. More than 30 years ago, he saw a woman die in that very same park in that very same neighborhood. He saw drugs and gangs and violence come into that neighborhood that he loved.  His aforementioned friend, Gregory Henderson, was shot and killed on July 7, 1995, not far from the spot where his One City youths were now wearing graduation caps and gowns. Caire made a vow that day to do something that would change the situations that were undermining and destroying the black community on Madison’s south side.

Kaleem Caire, founder and CEO of One City Schools, celebrates with Kailani Race at Penn Park. Kailani will start first grade at One City next fall.

“So many people I know who grew up in that area that didn’t reach their full potential and here we are holding the first-ever graduation of some young kids to have a bright future,” Caire says. “It was truly powerful.”

Graduation day – July 30th – was Caire’s birthday, just like it was his birthday four years ago when he first launched One City Schools because he wanted “to cultivate healthy, happy, thoughtful, and resourceful children who have the capacity and commitment to empower others and change the world, their families and communities for the better.”

One by one, kids names were called and they proudly went up to receive their diploma at the One City kindergarten graduation ceremony. “The energy was great. Parents were so proud,” Caire says. “You’ve seen the energy in this school … it is always great. As the school has grown and more and more students are coming and our team has really gotten into the grove of what we do, it’s just been amazing.

“The graduation was no different,” he adds. “To see all those kids in their cap and gowns at Penn Park and their families cheering them on … that was something special.”

Marlo Mielke, vice president and center director of One City, and Bryan Grau, principal of the One City Senior Preschool, present graduation certificates to young people at Penn Park.

Marlo Mielke, vice president and center director of One City, and Bryan Grau, principal of the One City Senior Preschool, greeted and congratulated each and every one of the students. Marilyn Ruffin, director of family and community initiatives, read Andreal Davis’s poem, “I Am Somebody.” 

It was a diverse crowd cheering on the students.

“We are mostly African-American, but we have everybody there – Latino, white, Asian,” Caire says. “And you saw that reflected in the graduation.”

Families – including many fathers – cheered on the young students. 

“People talk about us not being able to get fathers involved in their kids’ lives or there just not being enough parent involvement. Everything we’ve had – including the graduation – over the last three years we get fathers to show up,” Caires says.

Caire says they had a One City Father’s Day event in the middle of June where over 50 fathers showed up. “We had over 70 mothers for Mother’s Day,” he says. “Where a dad wasn’t available or couldn’t make it, we had somebody from our male staff stand in so that our kids had somebody stand in for them.

“This graduation was more of the same. To see all the fathers and mothers there … aunts and uncles,” Caire adds. “People say you can’t get parents involved in their children’s education. You can, but you just can’t be always calling them just when something’s wrong. You have to have these positive events and celebratory environments … especially for people who living day-to-day and struggling. We need to inspire.”

Caire remembers that people, too, did struggle in that same neighborhood while he was growing up there, but there was also a lot of love.

“We thought we grew up in the greatest neighborhood. We all loved each other and there were black kids all over the place,” he remembers. “But we had Latino and white kids. We all knew each other.”

When drugs started to come into the neighborhood in the mid-80s, that’s when things took a turn for the worse.

“People have always looked at South Madison a little curiously because there were people of color there, but to us, it was our home,” Caire says. “To see it just go away from what it once was in the mid-80s … that hurt. But in the last 7-10 years, the neighborhood has been slowly coming back. We think that our school, along with the Boys and Girls Club, being there, is a big part of that.”

After decades of being down, the south side is on the up and up. And One City, right down the street from where Caire grew up, is right in the middle of it.

“We want to see One City as an anchor of economic development,” he says. “People will see this as a sign that the neighborhood is coming back.  

“The energy that we’re helping to bring back to that southside corridor you could see in that graduation ceremony,” he adds. “Next year, my hope is that we will publicize this more widely … because we want the whole city to see our kids graduate.”